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RESEARCH ARTICLE
Contents Vol 67(3)

Selective Cleavage of Carbamate Protecting Groups from Aziridines with Otera’s Catalyst

Shan Sun A , Ilaria Tirotta A , Nicholas Zia A and Craig A. Hutton A B
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Melbourne, Vic. 3010, Australia.

B Corresponding author. Email: chutton@unimelb.edu.au

Australian Journal of Chemistry 67(3) 411-415 https://doi.org/10.1071/CH13464
Submitted: 3 September 2013  Accepted: 16 October 2013   Published: 11 November 2013

Abstract

Otera’s distannoxane catalyst was found to promote the cleavage of carbamate groups from N-protected aziridines. This method enables the chemoselective cleavage of an aziridinyl N-carbobenzyloxy (Cbz) group in the presence of other N-Cbz groups. The selectivity is due to the longer, weaker N–C bond of aziridinyl carbamates, as inferred through IR and crystallographic analyses.


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